Chris Ogboke: Turning Access Into Experience with Squeez

Founder of
Squeez
Chris Ogboke is a serial entrepreneur, growth strategist, and former pro athlete. With over 15 years of experience in startups and corporate innovation, he’s built his career around helping people get access to what matters. His latest venture, Squeez, tackles a familiar frustration: when you want something last minute—like a great restaurant or a tee time—and hear, “no availability.” Squeez brings a new model of access, where texting the owner like a VIP is just one digital handshake away. In this interview, Chris shares how his background in recruiting helped him build a strong advisory board, why valuing time is the next big frontier in consumer tech, and how a near-miss driving home from golf inspired a mission-driven startup.
Interview
Oct 16, 2025

Tell us how the idea for Squeez was born.

The idea came from a universal experience—trying to get into a good spot last minute and being told “no.” It’s frustrating. The place is probably half-empty, the line is long, or no one answers the phone. But here’s the truth: we’re all willing to pay for access, convenience, or time. The problem is only people with connections can text the owner and get what they want.

I needed to make that available to everyone. So we built Squeez: a way to digitally “shake hands” with the business and unlock VIP-style access. Businesses get paid fairly, and consumers get a better experience. It’s a win-win.

What’s the core problem you’re solving right now?

We’re helping businesses give customers the right and the ability to pay for what they value—not just a product or service, but a better experience. Consumers aren’t just looking to book something—they’re looking to feel seen, prioritized, and taken care of. And they’re willing to pay for that.

Who is your typical user today? Are they tourists, locals, or business clients?

As people, we can wear those three hats simultaneously, on the same day, or even the same evening! Imagine — in most cities, if you are looking to secure something nice, as a local, for a business dinner, without relationships, you may begin to feel like a tourist, pretty quickly!

What insights have you gained from observing what people are truly willing to pay for when it comes to access and time?

Convenience matters. This really is like Amazon Prime for access. You can use it, or find something else. That’s the beauty of a free market.

Does Squeez have an internal reputation or “social credit” system for users, similar to how loyal customers are recognized?

Yes, thanks to discovery calls with the CEO of an upscale, casual dining restaurant, we came up with valet access – a way for regulars to have no issues getting into the local, busy spots that they are approved for.

Which user acquisition channels work best for you — SMM, referral programs, or partnerships

Have you ever had a friend who seems to be really connected? Life is just easier when you have that type of friend. In a business perspective, we are no different. This is why we focus on partnerships. As Squeez is more of a middleware, not a marketplace - we integrate into existing customer journeys and existing technology to provide the most seamless offline access possible.

What trends are shaping your industry right now?

Hospitality is going through a soft patch in the U.S., but people are still spending—especially on experiences. That’s the key: people want time and space with people they care about. The product or location matters less than how it fits into their life.

If you can help someone create access to meaningful moments more easily, you’re solving a much bigger problem than it might seem on the surface.

How did you build your advisory board?

I come from a recruiting background, which shaped my approach. First, I start with the “why.” Then I filter ruthlessly—just because someone has a big-name logo on their résumé doesn’t mean they’re a fit.

I listen for passion, not polish. People often reveal their depth by what they don’t say. After that, I look into their informal network and backchannel references. It’s about aligning values, not just stacking resumes.

What’s your long-term vision for Squeez?

I see offline access becoming a new form of luxury. Whether it’s your local barber, a yoga studio, or a breakfast spot, people will increasingly expect to pay for convenience and certainty.

We’re creating a world where “no” is just the starting point—not the end. And Squeez is how you skip the line or secure access, without stepping on anyone’s toes.

What’s the most valuable lesson you’ve learned as a founder?

The world has all the answers—you just have to be curious enough to look and listen. For example, I sometimes play golf 40 minutes from home. The tee time experience sparked a business idea… but on the drive back, I nearly fell asleep at the wheel.

I’ve got two young kids at home and one in college. That day could’ve ended very differently. It made me realize how precious time is—not just to me, but to the people who rely on me. If my wife can pay a few extra dollars for me to finish earlier and be home, and be present with the family, or even be useful around the house, that’s worth more than any “deal” or “discount.”

Squeez is about helping people reclaim that kind of time, safely and meaningfully.

Does the “Squeez model” apply beyond restaurants and golf?

Absolutely. The philosophy of earning access through respectful digital connection is universal. Whether it’s wellness, beauty, fitness, or even healthcare, the idea is the same: if someone wants access and is willing to work or pay for it, there should be a clean, trusted way for businesses in our free market to say yes.

Are you currently fundraising or looking for partnerships?

We bootstrapped the early days and proved the concept lean. Now we’re looking for strategic partners—especially in fintech or experience-focused sectors—who share our values and passion for businesses and consumers. Grants in the digital well-being and time-management space are also part of the roadmap.

Squeez

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